First 90 Days as a CTO
First 30 Days: Learn & Assess
1. Understand Business Goals & Strategy
- Meet with the CEO, leadership team, and key stakeholders.
- Learn about the company’s mission, vision, and financials.
- Understand how technology supports business objectives.
2. Assess the Technology Landscape
- Review existing architecture, infrastructure, tech stack, and scalability.
- Identify technical debt, bottlenecks, and security risks.
- Evaluate ongoing projects and upcoming releases.
3. Engage with the Engineering Team
- Build relationships with key engineers and managers.
- Understand team structure, culture, strengths, and weaknesses.
- Assess engineering practices, development workflows, and technical debt.
4. Understand Product & Customer Needs
- Engage with product managers and understand the roadmap.
- Learn about customer pain points and gather feedback.
- Identify gaps in the product and technology strategy.
Days 31-60: Plan & Strategise
5. Define Your Technology Vision
- Align your vision with business objectives and growth plans.
- Define key technology priorities (e.g. scalability, security, AI adoption).
- Outline a high-level strategy for improvements and innovation.
6. Evaluate the Team & Processes
- Identify skill gaps and potential hiring needs.
- Assess whether Agile, DevOps, and CI/CD practices are optimised.
- Recommend improvements for engineering productivity and collaboration.
7. Ensure Security & Compliance
- Conduct a security audit to identify vulnerabilities.
- Ensure compliance with industry standards (GDPR, ISO 27001, SOC 2).
- Establish or refine cybersecurity policies.
8. Stakeholder Communication & Quick Wins
- Present findings and recommendations to the leadership team.
- Identify and execute quick wins to build credibility.
- Foster alignment between product, engineering, and business teams.
Days 61-90: Execute & Deliver
9. Build the Roadmap & Start Execution
- Develop a technology roadmap with clear priorities.
- Start tackling key technical debt and process inefficiencies.
- Launch key initiatives that align with business objectives.
10. Strengthen Culture & Hiring Strategy
- Set a strong engineering culture with best practices.
- Define hiring needs and attract top talent.
- Improve retention by fostering a collaborative, innovative environment.
11. Measure & Iterate
- Establish key metrics (e.g. uptime, deployment frequency, lead time).
- Monitor progress and adjust strategy based on results.
- Provide regular updates to the CEO and stakeholders.
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